Hydrochloric Acid → 2-(m-Methylbenzylthio)-5-trifluoromethylbenzoic acid

HRID 978086ノート

反応式

HRID 978086 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][SH:6].[CH3:10][O-:11].[Na+].Cl[C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:15]=1C#N.[OH-:26].[Na+].Cl>CN(C)C=O.C(O)C.O>[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][S:6][C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:15]=1[C:10]([OH:26])=[O:11]

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 676042-Chloro-5-(trifluoromethyl)benzonitrileHCID 2801207(3-Methylphenyl)methanethiolHCID 10942334Sodium Methoxide

生成物 1

HCID 202050722-(m-Methylbenzylthio)-5-trifluoromethylbenzoic acid

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒2 回HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
-15 °C

実験手順

A mixture of m-methylbenzylmercaptan (3.36 g, 24.3 mmol), sodium methoxide (1.31 g, 24.3 mmol) and N,N-dimethylformamide (12.5 ml) was cooled to -15° C., and then added dropwise with stirring to a solution of 4-chloro-3-cyanobenzotrifluoride (5.0 g, 2.43 mmol), in N,N-dimethylformamide (7.5 ml). After stirring for 1 hour at room temperature under a nitrogen atmosphere, the mixture was added to cold water (175 ml) and extracted with chloroform. The organic extract was dried (sodium sulfate) and evaporated to give a pale yellow oil, which was taken up in ethanol (10 ml) and 20% aqueous sodium hydroxide (45 ml) and heated at reflux temperature for 24 hours. Concentration of the reaction mixture followed by diethyl ether extraction and evaporation gave an orange-red oil, that was suspended in water and acidified with 6N hydrochloric acid. The solid that separated out was filtered and dried by suction. The solid was recrystallized from diethyl ether; yield 5.95 g (75%). The 60 MHz NMR spectrum in chloroform-d was in accord with the desired structure.

後処理

  1. additionadded dropwise
  2. extractionextracted with chloroform
  3. extractionThe organic extract
  4. dry with materialwas dried (sodium sulfate)
  5. customevaporated
  6. customto give a pale yellow oil, which
  7. temperatureat reflux temperature for 24 hours
  8. extractionConcentration of the reaction mixture followed by diethyl ether extraction and evaporation
  9. customgave an orange-red oil, that
  10. customThe solid that separated out
  11. filtrationwas filtered
  12. customdried by suction
  13. customThe solid was recrystallized from diethyl ether

出典と根拠

ORDレコード
ord-ec5c763e6fb54b21be25725941da1322
出典データセット
uspto-grants-1987_05
特許番号
US04663344

反応ノート

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